Polyoxyalkylenepolyols and process for producing ring-opened polymer

a technology of polyalkylene and polymer, which is applied in the preparation of organic compounds, sulfur dyes, group 5/15 element organic compounds, etc., can solve the problems of low reactivity of polyols with isocyanate groups in isocyanate-containing compounds, insufficient reactivity, etc., and achieves excellent adhesion, high reactivity with isocyanates, and high reactivity. , the effect of reducing the number of oxidized compounds

Inactive Publication Date: 2003-03-11
SANYO CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

Thus, urethane resins derived from the polyol composition (III) and/or polyol composition (II) of the present invention are characterized in that the reactivity with isocyanates is high in the step of production thereof, and that the humidity dependency of resin characterist

Problems solved by technology

Therefore, such polyols have insufficient reactivity for use as polyol components for thermosetting resins.
For example, they have low reactivity with isocyanate groups in isocyanate-containing compounds (tolylene diisocyanate etc.) and have insufficient reactivity when they are used as polyol components for urethane resins.
However, since the polyethylene oxide portions are hydrophilic, such method reduces the hydrophobicity of polyoxyalkylene polyols.
When such polyols are used, there arises a problem in that the physical and other characteristics of the resulting urethane resins vary widely depending on humidity.
However, this method of producing ring-opening polymerization products, which comprises effecting ring-opening polymerization of carbonates, thiocarbonates, dithiocarbonates and

Method used

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  • Polyoxyalkylenepolyols and process for producing ring-opened polymer
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  • Polyoxyalkylenepolyols and process for producing ring-opened polymer

Examples

Experimental program
Comparison scheme
Effect test

example 1

A 200-ml SUS autoclave equipped with a stirrer and temperature control device was charged with 58.1 g of glycerol-propylene oxide adduct with a molecular weight of 1,000 (Sannix GP-1000, product of Sanyo Chemical Industries) and 0.97 g of tris(pentafluorophenyl)borane. Then, 110.1 g of propylene oxide was added dropwise over 12 hours at a reaction temperature of 70-80.degree. C. Thereafter, the mixture was matured at 75.degree. C. for 6 hours and then neutralized with an aqueous solution of sodium hydroxide. Then, 3.0 g of synthetic silicate salt (Kyowaad 600, product of Kyowa Chemical) and water were added, and the mixture was treated at 60.degree. C. for 3 hours. The mixture was taken out of the autoclave, filtered through a 1-micron filter and then dehydrated, to give 161.3 g of liquid-form polyoxypropylenetriol (molecular weight: 3,000). The yield was 97% as calculated based on the weight of glycerol-propylene oxide adduct plus propylene oxide charged. The polyoxypropylenetriol ...

example 2

A 200-ml SUS autoclave equipped with a stirrer and temperature control device was charged with 58.1 g of glycerol-propylene oxide adduct with a molecular weight of 1,000 (Sannix GP-1000, product of Sanyo Chemical Industries). Thereto was added dropwise 110.13 g of propylene oxide and 0.0008 g of tris(pentafluorophenyl)borane over 12 hours at a reaction temperature of 714 80.degree. C., and the resulting mixture was matured at 75.degree. C. for 6 hours. Then, 3.0 g of synthetic silicate salt (Kyowaad 1000, product of Kyowa Chemical) and water were added, and the mixture was treated at 60.degree. C. for 3 hours. The mixture was taken out of the autoclave, filtered through a 1-micron filter and then dehydrated, to give 161.3 g of liquid-form polyoxypropylenetriol (molecular weight: 3,000). The yield was 97%. The polyoxypropylenetriol obtained had a hydroxyl value of 56.1.

The results of .sup.1 H-NMR chemical shift measurement in terms of .delta. values of the polyoxypropylenetriol obtai...

example 3

The procedure of Example 1 was followed in the same manner except that 87,1 g of glycerol-propylene oxide adduct with a molecular weight of 3,000 (Sannix GP-3000, product of Sanyo Chemical Industries) was used in lieu of the glycerol-propylene oxide adduct with a molecular weight of 1,000, and that tris(pentafluorophenyl)borane and propylene oxide were used in an amount of 0.97 g and 87.1 g, to give 169.0 g of liquid-form polyoxypropylenetriol (molecular weight: 6,000). The yield was 97%. The polyoxypropylenetriol obtained had a hydroxyl value of 28.1.

The results of .sup.1 H-NMR chemical shift measurement in terms of .delta. values of the polyoxypropylenetriol obtained (solvent: CDCl.sub.3) are shown below.

.sup.1 H-NMR, .delta. values: 1.11 (s, 305.6H), 2.5 (s, 3H), 3.20-3.79 (m, 310.6H)

The proportion of terminal primary hydroxyl groups was determined by the .sup.1 H-NMR method described hereinabove and found to be 74%.

The measurement results for .sup.1 H-NMR chemical shift .delta. ...

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Abstract

A polyoxyalkylene polyol or monool (I) of the general formula (1) below, in which not less than 40% of the terminally located hydroxyl-containing groups, namely -AO-H groups, are primary hydroxyl-containing groups of the general formula (2) below, or;a method of producing ring-opening polymerization products, by subjecting a heterocyclic compound to ring-opening addition polymerization with an active hydrogen-containing compound, using as a catalyst tris(pentafluorophenyl)borane, tris(pentafluorophenyl)aluminum, etc.

Description

The present invention relates to polyoxyalkylene polyols or monools having the proportion of terminal primary hydroxyl groups of not less than 40%; to a method of preparing ring-opening polymerization products by ring-opening addition polymerization of a heterocyclic compound; and to polyol compositions for use as polyol components for polyurethane resins, epoxy resins and like thermosetting resins. More particularly, it relates to polyoxyalkylene polyols having increased reactivity with isocyanato groups or the like without impairing their hydrophobicity; to a method of effecting ring-opening polymerization of cyclic compounds in the presence of a specific catalyst; and to the use of said compounds as polyol components for thermosetting resins.Polyols such as polyoxyalkylene polyols obtained by ring-opening reaction of a monoepoxide, such as an alkylene oxide, with an active hydrogen-containing compound are in wide use as starting materials for thermosetting resins such as polyuret...

Claims

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Application Information

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IPC IPC(8): C08G65/00C08G65/26C08G65/12C08G18/00C08G18/66C08G18/48C08G65/332C08G18/44C08G18/46C08G18/50C08G18/52C08G64/02C08G65/333C08G65/334C08G75/00
CPCC08G18/4812C08G18/4841C08G65/12C08G65/2654C08G18/6674C08G2101/0083C08G2110/0083
Inventor SATAKE, MUNEKAZU
Owner SANYO CHEM IND LTD
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